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Indium controlled regioselective 1,4-alkylarylation of 1,3-dienes with α-carbonyl alkyl bromides and N-heterocycles

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Abstract

We here describe a new, selective indium-promoted silver-mediated intermolecular oxidative 1,4-alkylarylation of 1,3-dienes with α-carbonyl alkyl bromides and N-heterocycles for producing functionalized N-heterocycles, which is characterized by its exquisitely controllable regio-/stereo-selectivity and excellent tolerance of functional groups. Mechanistically, the formation of the carbonyl-coordinated η3-allyl-In complex radical intermediate is the key factor for successfully achieving regio- and stereo-selectivity toward 1,4-difunctionalization and (E)-isomers.

Graphical abstract: Indium controlled regioselective 1,4-alkylarylation of 1,3-dienes with α-carbonyl alkyl bromides and N-heterocycles

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Article information


Submitted
14 Nov 2019
Accepted
16 Dec 2019
First published
16 Dec 2019

Chem. Commun., 2020, Advance Article
Article type
Communication

Indium controlled regioselective 1,4-alkylarylation of 1,3-dienes with α-carbonyl alkyl bromides and N-heterocycles

C. Gu, X. Ouyang, R. Song and J. Li, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08903A

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